A first — for Purrrrvert

Update: My song of love for both the Big Bad Cat and anal sex was Fleshbotted by the lovely Madeline. You’re such a love, Mads. Thank you!

It was the first time it’s ever happened to me, did you know that?

Anal sex I have had by the bucketload. (Although the imagery doesn’t work, the quantities do, trust me.) Until I met you, it was always accompanied by a certain amount of butt-clenching pain, and agony, prior to the experience dissolving into the fabulous sensation of having my ass ploughed.

I’ve had big cocks and small cocks in my ass. Small as in length — every woman knows that size only matters when you speak of girth, not length, but go tell that to a man. They never listen. You might listen, since you are who you are — and I love you immensely for that alone — but you don’t need to hear it, because you have no such insecurity. I’ve had men who knew what they were doing, and men who didn’t — although technically, anything that happened with the latter group cannot be termed anal sex, since as soon as I realised that they were clueless, I threw them off me and we moved on.

I’ve enjoyed anal sex — usually eventually, rather than the whole way through — in reality. In fantasy, it has sent me over the edge into the rainbow abyss of fabulous multiple orgasmic delight many a time.

But this was the first time that I came.

How you managed to hit my g-spot through the membrane that separates it from my anal passage; how you took the time to find the exact correct angle to which you needed to apply pressure; how you made me come over and over before that so that I was poised ready for another; how you carefully and diligently fucked me until i literally burst with joy, flooding the sheets and shaking as though I’d had a TENS unit applied to my clit (we’ll do that next time, darling 8-)); how you knew what and how to do what you did to me… I don’t know how you knew, or how you always know.

You know just how to touch me — whether with a gentle hand or an evil, bendy cane. You know the words to say. You know the songs to sing. You know how to surprise and delight me with unexpected purple rain. You have a wealth of knowledge that many would envy, and which is the admiration of all who witness it.

I’m so lucky to have you in my life. So very blessed. Thank you, my darling.

I’m a male-to-female transgendered person. I live my life as an out-of-the-closet sissy who dresses full-time en femme (i.e., wearing obviously feminine clothing). I haven’t had surgery and I’m not on hormones, but I’m naturally feminine-looking for a male.

Because I don’t have a vagina, receiving anal sex is for me the regular way in which I have intercourse with the men I’ve been with. So I can’t compare it to what it’s like to be on the receptive end of vaginal sex. But just as women have their Gräfenberg spot, the male homologue is the prostate, and unlike with you wherein your G-spot is separate from your rectum, with me the head of my men’s penises are able to directly stimulate my prostate during anal sex.

I remember when I had my first anal orgasm, i.e., an orgasm deriving from my prostate instead of from my penis. At the time I was age 23 (I’m now 31 years of age) and my lover was a black man around age 45. His penis was about 8” in length, and it was very thick. I’ve had much longer penises before, but as you mention, it’s the girth of a man’s penis that’s more important.

When it happened it felt like a full-body orgasm, with intense waves of orgasmic pleasure coursing from my male G-spot and spreading all over my body. My entire body shook uncontrollably while my legs were wrapped around my man’s torso as he continued to hump me. The sensation was unlike anything I’ve felt before. Not only was it very intense, but it was also a truly feminine feeling, as well. My penis didn’t ejaculate semen, although it was leaking precum. It was a very wonderful sensation.

Sort of analogous to what Fantasia said, I haven’t actually yet cum from anal sex (in the sense of ejaculating semen from a penile orgasm) without my penis being stroked (and of course, the penis is the male homologue of the clitoris). Although during a good dicking I often reach a state that feels like I’m right on the ege of having a penile orgasm and about to ejaculate (i.e., without any stimulation applied to my penis), which feels exquisite. My current boyfriend is pretty good at making me feel like that. Although I do leak precum like crazy when my boyfriend fucks me, during which time it only requires a little stimulation applied to my penis in order for me to have a penile orgasm. One of my favorite things is when my boyfriend continues to dick me after I’ve shot off–I love the feeling of being thoroughly fucked by him.

No such words are needed with me, Fantasia, as I know very well what you mean. And besides, if such words existed then they would only have real meaning for those who have experienced such a state.

Having ones legs spread and being worked-over, and over again, by one’s competent man–is there a word for that? And if there were, what meaning would it hold for those who hadn’t experienced it?

Being an open sissy-fag, many people look upon me with derision. I’m not a genetic woman, and yet I’m not much of a man. I’m what some wisecrackers call a “cum-catcher.” Which is an interesting epithet, since aren’t all mothers “cum-catchers”? What do such terms say about how many men regard women, such that they would (ignorantly) disparage their own mothers by thowing out such remarks? Yet such comments are the standard fair among many cliques of popular culture.

And so this idea exists that males can’t be feminine. But even worse, to be feminine is to be debased, as then one is a “cum-catcher,” or some similar term. Think about that. The idea exists within the zeitgeist that women are something debased: femininity is a state to be avoided, unless one was genetically born with the infliction, in which case it can’t be avoided.

Masculine genetic females are for the most part tolerated by society because they are regarded as attepting to lift themselves up. What derision occurs is due to the thought that they’re attempting to bite off more than they can chew by attempting to take on a masculine role.

Indeed, within a number of forms of pop-culture, women dressing like men is fairly common, such as within hip-hop culture (e.g., baggy shirts and jeans).

But when a boy wants to be feminine, then people become aghast. Because then he’s degrading himself by wanting to be like a woman. He’s thereby lowering himself–he’s giving up his higher status for a lower status. And that is just unthinkable.

So I’ve had to overcome a lot of self-hate and self-loathing in order to accept my feminine self. I’ve had to overcome a lot of societal disapproval in order to accept myself.

Indeed, I used to think of myself as all-man. At least I tried to. I tried to make myself butch. But eventually my feminine-self made herself known, whereupon I came out to my mother at age 23, and a bit after that to the world. Thankfully my mother accepts me fully.

How that relates to the topic of our discussion is that I’ve experienced sex both ways, i.e., as a male making love to a woman, and as a feminine person being made love to by a man.

From my experience, feeling sex as the receptive partner is much more intense, because as the feminine, receptive partner one opens onself up and lets oneself go–at least when one goes all the way. Now, let me explain that latter statement, i.e., regarding going all the way. Before I explain that, let me relate the case of the male role in sex. The male can’t fully let go during sex. Even if the female is riding him and doing all the work, he at the very least must maintain an erection–even if that’s not a conscious action on his part, it still must occupy some sector of his mind. And so, during male-penetrative sex, the male has no choice but to be engaged in world, i.e., in the here and now. It’s not really possible for him to fully let himself go.

Now contrast that with the receptive partner. She has no erection to maintain. She doesn’t have to be engaged with the world. She can fully let herself go, and completely take in the sensations she’s experiencing. She can concentrate on the sensations, while drowning everything else out. And because she already accepts her feminine aspect, she can spread her legs in order feel the fulness of her man’s shaft working back and forth within her. To feel it working her over into a rhapsodic climax.

And to do that over, and over again. It’s that ineffable experience which you’re speaking to, Fantasia, and which I well-understand, even if I can offer no word to encapsulate it, since I’m not aware of a word invented that really conveys that experience.

So with me, receiving anal sex from my boyfriend is a truly intense feminine treasure. It’s an experience I wouldn’t trade for the world. The feeling of being opened-up within one’s most intimate place, and to just take it all in while fully letting go. To be dicked and dicked well. That’s such a lovely experience.